


5 Times Mimi Was the Best Wing(wo)man + 1 Time Daisuke Handled His Own Love Life

by Anatui



Category: Digimon - All Media Types, Digimon Adventure, Digimon Adventure Zero Two | Digimon Adventure 02, Digimon Adventure tri.
Genre: Attempted Seduction, Clueless Ichijouji Ken, College/University, Declarations Of Love, Drinking Games, Drunken Flirting, Drunken Kissing, Friends to Lovers, Fuck Marry Kill, High School, House Party, Idiots in Love, Kissing Games, M/M, Motomiya Daisuke | Davis Motomiya Is a Bi Disaster, Never Have I Ever, Odaiba Day, POV Outsider, Seven Minutes In Heaven Game, Sexual Humor, Smitten Motomiya Daisuke | Davis Motomiya, Summer Vacation, Taboo Drinking Game, Team Bonding, Team as Family, Truth or Dare, Underage Drinking, Wingman Tachikawa Mimi, Would You Rather?
Language: English
Status: In-Progress
Published: 2020-04-05
Updated: 2020-04-06
Packaged: 2021-03-01 04:48:34
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,754
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23459641
Author URL: https://archiveofourown.org/users/Anatui/pseuds/Anatui
Summary: "Okay, let's play a game," Mimi said.The response could've used much improvement. Far too many of her friends groaned, but the grin on Daisuke's face outweighed them all. He had so much faith in her, and she refused to let him down."It's really simple," she promised. "You choose someone to ask which of two equally good or equally bad items they'd rather do, and you have to answer honestly. Then the person who answered gets to choose the next person and so on until everyone has gone." Her gaze darted around the group. "Daisuke-kun, you played when you visited me in New York. Why don't we go first?"He nodded. "Let's do it.""Okay." She grinned. "Daisuke-kun, would you rather have amazing sex every day but never be able to keep a relationship or spend the rest of your days with the love of your life but remain a virgin forever?"Daisuke scowled at her. "Come on, Mimi. They're notallsupposed to be sexual."ORWhen his attempts to show Ken how much he cares fail, Daisuke seeks out Mimi's help, and she is determined to be the Best Wing(wo)man Ever. If she happens to go a bit overboard, it's all in the spirit of love and romance.
Relationships: Ichijouji Ken/Motomiya Daisuke | Davis Motomiya, Motomiya Daisuke | Davis Motomiya & Tachikawa Mimi
Comments: 8
Kudos: 26
Collections: Ana's 2020 Writing Challenge, Daiken 5+1 Challenge, Daiken Discord Server





	1. Introduction

**Notes for the Chapter:**

> Okay, this 5+1 is turning out far longer than I anticipated, so I decided to post it in parts. The first chapter is simply the introduction, and then there will be six subsequent chapters that will be the five and plus one.

" _Please!_ "

Lips pursed, a hand on her hip, Mimi tapped the foot of her pink Louis Vuitton stiletto on the tile floor. If she wanted to milk this for all it was worth, it would be easy.

But well, she couldn't help but take pity on him.

Nearly eighteen years old, but Daisuke still hadn't managed to curb his melodramatic streak. And he obviously wasn't above begging.

Mimi groaned, and finally, her foot stopped. "How am I supposed to help, Daisuke-kun? I barely know him." She reached down, grasped him by the arm, and dragged him to his feet—in her pumps, she was a good five or six centimeters taller than him. "Really, you're making this harder than it needs to be."

Instead, he slumped against the wall nearby. "I don't know what to do anymore. I've tried to be subtle, I've tried to be obvious, but no matter what, he doesn't even react."

She sighed. "Have you considered that Ichijouji-kun isn't interested?"

Daisuke instantly deflated.

Oh, he'd definitely considered it.

Mimi instantly backtracked—everyone could tell Ken was open to the idea at the very least. "Why haven't you asked Taichi-san for help? Or Koushiro-kun?" She frowned. "Hell, Yamato-san would probably have some good advice too."

He looked up, barely catching her eye before his gaze fell to the floor again. "Have you met them? Yamato-senpai is the only one who's got any game, but I doubt he had to convince Sora-san to go out with him. Plus, I don't think advice on bedding groupies would be helpful with Ken."

She snickered. "No, I wouldn't imagine so."

Daisuke took a deep breath and finally met her eyes again; this time, a deep determination burned in his brown orbs. "Look, all I need is a little push. A nudge in the right direction." He chewed on his lip, then added, "Opportunity."

She looked him up and down, slowly assessing him, but it was the eyes that convinced her.

Mimi sighed. "All right, fine." She leaned against the wall beside him, arms crossed over her chest, her bottom lip between her teeth. "You know, it's almost August 1st—I've been considering throwing together a sort of party. Something a bit more extravagant than the picnic we normally do—I swear, nobody knows how to plan these sort of things but me."

His bushy eyebrows shot up curiously.

Then, she grinned. "Make sure you clear your schedule for the weekend—and everyone else. Oh hell, for the whole week. We're going to my family's cabin in Okinawa."

*

The cabin in Okinawa was something her parents had refused to sell when they moved to New York, and when she returned during her first year of high school, she made sure to vacation there a couple times a year to make proper use of it and to keep it in working order.

And now she had a better use for it than ever before.

Daisuke had come to her for help. Of all the people he could have asked, he'd come to _her_. And she was going to do everything in her power to make sure he had as high a chance of wooing Ichijouji Ken as possible.

She planned everything out to the letter.

From the flight to Okinawa and the room assignments to the games they'd play during their week-long stay, she had everything set up perfectly, and she wasn't going to let anything ruin her success.


	2. Would You Rather?

**Notes for the Chapter:**

> Okay, let's get started...

"Welcome!" Mimi cried, clapping her hands together as the group trudged inside the door.

Her eyes scanned the main living space, making sure the open area had been properly cleaned in preparation for their arrival. She released a pleased sigh upon confirming everything was in order, and when Taichi and Daisuke and their Digimon investigated the kitchen, she discovered even the fridge had been stocked—she needed to make sure they gave Ba-chan a good bonus this year.

"Hey, you two, get back in here," she snapped, waving those idiot goggle boys back into the main living room with the rest of the group. "Let's get everyone settled in before we eat something, okay?"

When the group gathered close, she studied each of them, going over the room assignments she'd decided in her head just in case anything needed adjusted.

"Ladies first," she announced, motioning for Sora, Miyako, and Hikari to follow her up the staircase and to the right.

Upstairs, she pushed open the door to her favorite room in the cabin—the largest in the house with the huge platform bed. "Sora-san," she said as she set down her own luggage at the foot of the bed, "you can stay with me. We've shared a bed before."

"It's super comfy," Palmon added with a grin.

Sora nodded and set her bag down as well, and Piyomon made itself comfortable on the bed to watch her unpack. "Of course, Mimi-chan."

"Now," Mimi continued, already heading out of the room, Palmon at her heels, "these are the only two rooms on this floor, so we won't have to worry about running into any boys in the middle of the night. There's a bathroom here"—she pointed out the next door on the left, then continued to the final door—"and this is where you'll stay, Hikari-chan, Miyako-chan."

This room was smaller, though it still had plenty of space for the two girls and their Digimon. Instead of one large bed, there was a twin-sized bed on each side, and Tailmon and Hawkmon each happily picked a side.

"Ah, thank you, Mimi-san," Miyako said, her eyes scanning the room.

Hikari beamed at her. "This looks great."

With another cheer of excitement, Mimi left them to unpack and returned to the group of boys downstairs.

Taichi was already lounging on the couch, flipping through television channels, with Yamato leaning against the armrest beside him, arms crossed over his chest as he chastised his best friend for turning on the television without asking first. Agumon and Gabumon in turn were hanging out on the couch together, happily talking while their partners bickered. Koushiro, Jou, and Iori were waiting patiently by their luggage and chatting quietly, their Digimon hanging about them and joining in on the conversation, and Takeru was looking through the kitchen, Patamon atop his head.

Where had Daisuke and Ken gone?

She frowned.

Well, no matter. She wanted to save them for last anyway. It would be a lot easier to get Ken to go along with it if he knew he didn't have any other options—besides, she seriously doubted he'd be comfortable sharing a room with anyone other than Daisuke.

She showed Koushiro, Jou, and Iori and their Digimon to a room with a set of bunk beds and one loft bed with a desk underneath. Koushiro would probably enjoy making use of the desk during their stay, and Iori would probably enjoy the opportunity to spend more time with those whose crests he shared.

The other room on that side of the cabin went to Taichi, Yamato, and Takeru and their Digimon, though the three guys paused at the sight of the large bed on one side and twin on the other. "I'll let you three figure out who sleeps where," she said in a singsong voice as she slipped away, knowing full well Yamato and Takeru would share the bed.

But Daisuke and Ken were still missing.

With a curious frown, she looked around the main floor—no one was in the bathroom and the bedroom she'd set aside for them remained untouched. Besides, their bags were still sitting in the living room, and V-mon and Wormmon were, of course, at their sides.

Hmm.

Mimi grabbed a can of coffee from the fridge and popped the tab as she considered.

Maybe those two idiots had gotten their heads on straight and were hiding somewhere to make out.

Hah.

Yeah right.

No, they'd probably stepped out for some completely normal, natural reason that had nothing to do with their obvious feelings for each other. Because they were idiots.

A moment later, the front door opened and closed a moment later, and their hushed voices carried through the main floor.

She took another drink of her coffee and walked around the island to reach the living room again. "There you are!" A bright smile spread across her face, and she grabbed each boy's wrist as they were sliding their house slippers back on and dragged them toward the remaining bedroom; V-mon and Wormmon followed at their heels. "Let's get you settled into your room."

The final bedroom was the smallest and featured one bed, big enough for two people, in the middle of the room, though there wasn't much else. As it was on the opposite side of the cabin from the other two rooms on the main floor, there was a certain amount of privacy—including a private bathroom.

"Cool!" Daisuke jumped onto the bed and immediately relaxed, dropping his house slippers on the floor in the process. "This is great, Mimi. So comfy." He spread his arms and legs across the mattress, eyes falling shut, and V-mon, quickly followed by Wormmon, joined him on the bed.

But Ken stood with wide eyes in the doorway as the blood drained from his face. "Wait, uh, Mimi-san, are you sure this is the best setup? Surely there are other options."

She considered him with a frown. "I'm sorry, Ichijouj-kun, but everyone else has already gotten their room assignments. Besides, I figured you'd be most comfortable with Daisuke-kun—you know, your best friend."

Any hope in his eyes crumpled at her words.

Daisuke lifted his head and glowered at him. "You saying you don't want to sleep with me, Ichijouji?"

Ken's previously white face lit up a warm pink, and as much as he tried to respond, no words came when he opened his mouth.

"Oh, give him a break, Daisuke-kun," Mimi chided. "You know he likes his privacy." She turned to give Ken a soft, reassuring smile. "I'll look around for a futon to lay out, all right? I'm sure we've got some around here somewhere."

He smiled appreciatively. "Thank you, Mimi-san," he said with a short bow. Only then did he enter the bedroom and sit on the edge of the bed. Wormmon gravitated to his side immediately.

But Daisuke curled on his side to look at him better. "What're you being so weird about? We've shared a bed before…"

Mimi stepped out, only to return a moment later with the luggage they'd left in the living room, but the two were sitting on the edge of the bed, side by side, and the atmosphere was thick with tension. Ken stared at his hands, cheeks a bright pink, and Daisuke sat beside him with a deep frown as the silence stretched between them and their Digimon looked on worriedly.

She decided to leave the luggage outside the door. Better not to disturb them.

*

The afternoon had been devoted to settling in. Each room had a closet and a dresser the guests could use for their clothes and other items, and everyone unpacked their things, though some of them put more time and effort into the task than others. Daisuke, for one, had dumped all his clothes into a drawer and called it good—Ken, of course, had gone through and folded his clothes after he'd put his own things away.

They had a late afternoon lunch of egg sandwiches and fruit and explored the surrounding area, and Mimi and Palmon were more than happy to give everyone a tour. Okinawa was a beautiful area, and the Tachikawas' house was on a nice private plot with a beautiful view of the ocean below. They even had a steep staircase leading down to the beach.

But the fun—at least as far as Mimi was concerned—didn't begin until the sun set.

"There's wood along the back wall," she said as she pushed Yamato and Gabumon toward the cabin again. The firepit in the backyard needed lit, and Yamato was probably the best for the job.

The group gathered on the cushioned couch and chairs around the firepit, their Digimon close at hand, while Mimi and Palmon ran around making sure everyone had snacks and drinks for a while. A small table at the edge of the patio housed more for when everyone ran out, and she made sure it was full before finally taking a seat beside Sora and Piyomon.

Nearly everyone in the group was there, but there was a notable absence of the two most important people. Really, how was she supposed to help Daisuke if he and Ken were never around?

Thankfully, they came out of the house not long later, V-mon and Wormmon at their heels. Daisuke was laughing, but Ken looked rather uncomfortable—Mimi was unsurprised when he leaned close to her from behind the couch to ask, "Ah, Mimi-san, have you found a futon for me to use?"

She tried not to laugh—his politeness and nervousness were endearing to say the least—as she turned to him. "Oh, I'm sorry, I forgot! I looked everywhere, but I couldn't find any in the house. They must've been taken to be cleaned."

His face fell. "Oh."

"Don't worry about it," she said, and a smile flashed across her features. "I'll call Oba-san tomorrow; I'm sure she knows what happened to them."

It was only a partial lie. Ba-chan definitely knew where the futons had gone because Mimi had insisted they be removed from the premises before everyone arrived. She had set up the rooms exactly how she wanted them, and she didn't want anyone getting out of their assigned places, thank you very much.

"Thank you, Mimi-san," Ken said, then swept around the couch to take a seat.

Daisuke had chosen the remaining large armchair, which definitely had enough space for a couple people, but Ken still hesitated, even as Daisuke made sure he had plenty of room and patted the seat beside him. The poor dear was so uncomfortable, so scared of everything, but he took the proffered spot and held Wormmon in his arms like his life depended on it, making sure to keep space between Daisuke and himself.

Hmm, no wonder Daisuke was so concerned.

But really, there wasn't anything to be worried about: Ken's discomfort probably stemmed from the fact that he had feelings for Daisuke, not because he didn't.

Maybe the game she had planned would help him relax more.

Then again, this was Ken, so maybe not.

Still, might as well try.

She clapped her hands together to gather everyone's attention. "Okay, let's play a game."

The response, of course, could've used much improvement. Far too many of her friends groaned, but the grin plastered on Daisuke's face outweighed it all. He had so much faith in her, and she refused to let him down.

"It's really simple," she promised, leaning back in her seat with a happy smile. "You choose someone to ask which of two equally good or equally bad items they'd rather do, and you have to answer honestly. Then the person who answered gets to choose the next person and so on until everyone has gone. On the next round, we can go in a different order." Her gaze darted around the group, and nine sets of curious eyes stared back. "Daisuke-kun, you played this when you visited me in New York. Why don't we go first?"

He nodded. "Let's do it."

"Okay." She grinned. "Daisuke-kun, would you rather have amazing sex all the time but never be able to keep a boyfriend or girlfriend or spend the rest of your days with the love of your life but remain a virgin forever?"

Daisuke scowled at her. "Come on, Mimi. They're not _all_ supposed to be sexual."

She giggled victoriously. "Just answer the question."

He fidgeted in his seat and leaned against the armrest, away from Ken. "Love of my life," he said in a quiet voice. "I would've thought that was obvious." Not that that stopped the pink blush that covered his cheeks.

Mimi chose to ignore him in favor of saying, "See? It's not so hard." She cast her attention back to Daisuke. "So, who gets to go next?"

He cast his gaze around the circle before finally settling a couple seats over. "Miyako, would you rather marry a complete stranger? Or marry your ex?"

She sent him a scowl. "Stranger."

Which, to be fair, Miyako had just broken up with a philosophy major a couple years above her at her university. The relationship had been quite serious during the two months it had lasted, and it had fallen apart quickly.

She moved on to the next person.

Several turns later, when Hikari turned to Ken, Mimi paid particular attention, her eyes scrutinizing the introverted boy with interest. "Ah, Ken-kun, who would you rather have read your diary—your parents or all of us?"

His face instantly turned bright red, and his answer was a mumbled, "Mama and Papa."

Daisuke frowned but remained silent.

Hmm, interesting.

Considering what she knew from Daisuke, that surprised her: Ken had started keeping a journal at the urging of his therapist, so she'd assumed he'd want to keep his depressed ramblings from his parents more than from the group. Daisuke had said his parents were particularly sensitive, after all.

So what was he writing about in his journal that he'd rather his sensitive parents read than his friends?

By the end of the first couple rounds, it was clear who was good at the game and who was just uncomfortable.

Yamato, when he joined them after he and Gabumon got the fire going well enough, was particularly vicious in his questions. Miyako approached the game with determined precision. Taichi had thrown himself fully into the let's-all-ask-embarrassing-sexual-questions game plan and was not willing to relent. Daisuke liked to ask the ridiculous questions, though Mimi had already known that, but they were usually oddly insightful.

Most of the others were either too nice or too timid to ask anything that was truly worthy of the game, but you couldn't exactly have some of the people not asking questions.

The real surprise was Hikari, though perhaps it shouldn't have been. Unfortunately, Mimi had spent much of Hikari's childhood in America instead of here, where she could be privy to the young girl's growth. Hikari, though, was sensible enough to approach each question in a different way depending on who her victim was. But while her questions shifted from soft to feisty, they were always probing.

Hikari could be a useful ally.

At the start of the fifth round, Mimi finally settled her eyes on Ken. "Ichijouji-kun," she said, catching him off guard. "You're sexting your crush or partner or whatever, but you accidentally send an explicit text to someone else. Who would you rather accidentally send it to—your boss or your best friend?"

Ken didn't even look at Daisuke before quickly saying, "I'd rather send it to my boss."

Beside him, Daisuke only looked more and more worried.

And there were definitely a few others around the circle who looked surprised by that answer, but if Mimi's theories were correct, it wasn't that surprising. Especially with the way Ken was continuing to put space between him and Daisuke.

In all the times she'd seen the boys interact in the past, they'd never seemed to stop touching each other and laughing in a cute, secretive way that had made them look like they were already a couple.

That definitely wasn't the case now.

Instead, Ken shied away—from Daisuke's attentions, from Daisuke's touch, from Daisuke's worried looks. And his answers so far were relatively indicative: He'd rather his parents see his innermost thoughts; he'd rather send an explicit text to his boss; he'd rather live alone forever than have a close friend as his roommate for the rest of his life. He kept away from Daisuke like getting too close would hurt him, and well, maybe it would.

The question was why.

And that was where her theories came in. Theories that needed confirmation more than anything else—confirmation before she could talk to Daisuke, before she could implement the next stage of her plan.

It was nearly midnight when the first people began to turn in, and the game wasn't nearly as fun after that. Ken, to no one's surprise, was one of the first couple people to leave, and he carried Wormmon inside the house after an uncomfortably formal goodbye, his posture stiff.

When the game fell apart once there were only five people left, Mimi slid into Ken's vacant spot on the chair with Daisuke, who'd stopped paying attention the moment Ken had left. "Talk to me," she said, shifting to look at him properly.

Daisuke's head shot up. "Huh?" He hadn't even noticed when she sat down.

"What are you so worried about, Daisuke-kun?"

He huffed, and his gaze slid back toward the cabin. "I don't understand. He's been so distant lately, and I don't know what to do."

Mimi pressed a comforting hand to his shoulder and smiled. "You'll get through this, and I promised I'd help you, remember?"

Daisuke turned big brown eyes on her, and her heart clenched. He looked so hopeless, and that was not a good look on Daisuke. She'd promised she'd help, and she intended to.

"Don't worry so much," she murmured. "I'm developing a plan as we speak."

"Thanks, Mimi-san."

Oh dear.

Things were worse than she thought. Daisuke never used honorifics with her anymore. He hadn't in years, not since the first time he visited her in New York—and he'd done that a couple times before she'd moved back to Japan in high school.

"Come on," she said, rising from the chair, tugging him up with her. "You should go to bed, get some rest."

But when they stood outside the room, Daisuke hesitated. V-mon had gone to bed not long after Ken and Wormmon, and that made him the last one to join them. And okay, sharing the bed with Ken when Ken wasn't particularly receptive to his friendship right now must seem a daunting task.

"Get some sleep," she said again, inclining her head toward the door. "Things will be clearer in the morning."

He nodded, and as he closed the bedroom door behind himself, she could only hope that was true.

**Notes for the Chapter:**

> Next time...they play Never Have I Ever


End file.
